Gelation-driven selection in dynamic covalent C=C/C=N exchange

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)6822-6828
Journal / PublicationChemical Science
Volume8
Issue number10
Online published6 Sep 2017
Publication statusPublished - 1 Oct 2017
Externally publishedYes

Abstract

Knoevenagel barbiturate derivatives bearing long alkyl chains were proven to form organogels in suitable solvents based on supramolecular interactions. Their reaction with imines allows for component exchange through C=C/C=N recombination. The effect of various parameters (solvents, chain length, and temperature) on the C=C/C=N exchange reaction has been studied. Mixing Knoevenagel compound K and imine I-16 in a 1 : 1 ratio generated a constitutional dynamic library containing the four constituents K, I-16, K′-16, and I′. The reversible exchange reaction was monitored by 1H-NMR, showing marked changes in the fractions of the four constituents on sol-gel interconversion as a function of temperature. The library composition changed from statistical distribution of the four constituents in the sol state to selective amplification of the gel forming K′-16 constituent together with that of its agonist I′. The process amounts to self-organization driven component selection in a constitutional dynamic organogel system undergoing gelation. This process displays up-regulation of the gel-forming constituent by component redistribution through reversible covalent connections.

Citation Format(s)

Gelation-driven selection in dynamic covalent C=C/C=N exchange. / Liang, Chunshuang; Kulchat, Sirinan; Jiang, Shimei; Lehn, Jean-Marie.

In: Chemical Science, Vol. 8, No. 10, 01.10.2017, p. 6822-6828.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal